#------------------------------------------------------------------------------
#$Date: 2024-04-10 02:30:59 +0200 (Wed 10 de Apr de 2024) $
#$Revision: 291153 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/31/7063141.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7063141
loop_
_publ_author_name
'Wang, Fei'
'Zhang, Yi'
'Zhou, Wei'
'Long, Zhiqing'
'Xiong, Shenglun'
'Zhang, Qinpeng'
'Sessler, Jonathan L.'
'He, Qing'
_publ_section_title
;
 “One--Pot” Synthesis of Oligopyrrolic Dialdehydes
;
_journal_name_full               'New Journal of Chemistry'
_journal_paper_doi               10.1039/D4NJ00933A
_journal_year                    2024
_chemical_formula_moiety         '2(H2 O), 2(C22 H26 N4 O2)'
_chemical_formula_sum            'C44 H56 N8 O6'
_chemical_formula_weight         792.96
_chemical_name_systematic        WF-3
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-02-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-10-03 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                105.506(6)
_cell_angle_beta                 102.442(6)
_cell_angle_gamma                90.015(6)
_cell_formula_units_Z            1
_cell_length_a                   8.6855(7)
_cell_length_b                   9.1540(9)
_cell_length_c                   13.8725(13)
_cell_measurement_reflns_used    4144
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      72.155
_cell_measurement_theta_min      5.018
_cell_volume                     1035.89(17)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_av_unetI/netI     0.0732
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5671
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.292
_diffrn_reflns_theta_min         5.023
_exptl_absorpt_coefficient_mu    0.695
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'dull brownish brown'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_preparation       CHCl3/n-hexane
_exptl_crystal_recrystallization_method CHCl3/n-hexane
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.089
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3985
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.1331
_refine_ls_R_factor_gt           0.1186
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1818P)²+1.4580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2934
_refine_ls_wR_factor_ref         0.3077
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3264
_reflns_number_total             3985
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj00933a2.cif
_cod_data_source_block           cu_20211202_wf_3_0m_5
_cod_database_code               7063141
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.934
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 H3A-H4
 2.52 with sigma of 0.01
 H1-H3B
 2.52 with sigma of 0.01
 H4-H3B
 2.52 with sigma of 0.01
3.a Free rotating group:
 O3(H3A,H3B)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C16(H16A,H16B), C19(H19A,H19B), C7(H7A,H7B)
3.c Aromatic/amide H refined with riding coordinates:
 N4(H4), N1(H1), C1(H1A), C11(H11), C12(H12), C22(H22)
3.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C17(H17A,H17B,H17C), C5(H5A,H5B,H5C), C20(H20A,H20B,H20C)
;
_olex2_submission_original_sample_id WF-3
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.2567(3) 0.7039(3) 0.5014(2) 0.0399(7) Uani 1 1 d G . . . .
H3A H 0.329849 0.777498 0.524160 0.060 Uiso 1 1 d DG U . . .
H3B H 0.181401 0.737356 0.461955 0.060 Uiso 1 1 d DG U . . .
O1 O 0.0962(4) 0.8669(3) 0.6578(2) 0.0452(7) Uani 1 1 d . . . . .
N4 N 0.3816(3) 0.4437(3) 0.3717(2) 0.0279(6) Uani 1 1 d . . . . .
H4 H 0.341616 0.509812 0.417145 0.033 Uiso 1 1 calc DR U . . .
N1 N 0.1189(3) 0.5442(3) 0.6241(2) 0.0278(6) Uani 1 1 d . . . . .
H1 H 0.159031 0.573859 0.578876 0.033 Uiso 1 1 calc DR U . . .
O2 O 0.4111(4) 0.7408(3) 0.3416(2) 0.0456(7) Uani 1 1 d . . . . .
N2 N 0.2492(3) 0.3323(3) 0.4966(2) 0.0278(6) Uani 1 1 d . . . . .
N3 N 0.2487(4) 0.0284(4) 0.4951(2) 0.0427(8) Uani 1 1 d . . . . .
C15 C 0.4568(4) 0.2266(4) 0.2805(2) 0.0295(7) Uani 1 1 d . . . . .
C2 C 0.0522(4) 0.6366(4) 0.6973(2) 0.0285(7) Uani 1 1 d . . . . .
C9 C 0.1134(4) 0.3986(4) 0.6322(2) 0.0266(7) Uani 1 1 d . . . . .
C10 C 0.1810(4) 0.2839(4) 0.5606(2) 0.0280(7) Uani 1 1 d . . . . .
C14 C 0.3840(4) 0.2914(4) 0.3615(2) 0.0286(7) Uani 1 1 d . . . . .
C21 C 0.4511(4) 0.4772(4) 0.3003(2) 0.0289(7) Uani 1 1 d . . . . .
C3 C 0.0025(4) 0.5482(4) 0.7540(2) 0.0298(7) Uani 1 1 d . . . . .
C18 C 0.4979(4) 0.3439(4) 0.2418(2) 0.0289(7) Uani 1 1 d . . . . .
C1 C 0.0437(4) 0.7970(4) 0.7082(3) 0.0339(8) Uani 1 1 d . . . . .
H1A H -0.007316 0.853240 0.759168 0.041 Uiso 1 1 calc R U . . .
C13 C 0.3157(4) 0.2321(4) 0.4315(2) 0.0281(7) Uani 1 1 d . . . . .
C4 C -0.0708(4) 0.6065(4) 0.8446(3) 0.0352(8) Uani 1 1 d . . . . .
H4A H -0.136996 0.523171 0.851194 0.042 Uiso 1 1 calc R U . . .
H4B H -0.140618 0.688250 0.832351 0.042 Uiso 1 1 calc R U . . .
C16 C 0.4829(4) 0.0612(5) 0.2380(3) 0.0387(8) Uani 1 1 d . . . . .
H16A H 0.523465 0.017391 0.295853 0.046 Uiso 1 1 calc R U . . .
H16B H 0.564991 0.053447 0.197454 0.046 Uiso 1 1 calc R U . . .
C6 C 0.0406(4) 0.3983(4) 0.7133(2) 0.0295(7) Uani 1 1 d . . . . .
C11 C 0.1780(5) 0.1291(4) 0.5589(3) 0.0354(8) Uani 1 1 d . . . . .
H11 H 0.125557 0.095632 0.603240 0.042 Uiso 1 1 calc R U . . .
C12 C 0.3171(4) 0.0782(4) 0.4324(3) 0.0369(8) Uani 1 1 d . . . . .
H12 H 0.368277 0.008934 0.387107 0.044 Uiso 1 1 calc R U . . .
C19 C 0.5749(4) 0.3319(5) 0.1529(3) 0.0368(8) Uani 1 1 d . . . . .
H19A H 0.640874 0.243115 0.146003 0.044 Uiso 1 1 calc R U . . .
H19B H 0.645311 0.423853 0.167356 0.044 Uiso 1 1 calc R U . . .
C7 C 0.0092(4) 0.2636(4) 0.7509(3) 0.0333(8) Uani 1 1 d . . . . .
H7A H -0.029535 0.174954 0.691092 0.040 Uiso 1 1 calc R U . . .
H7B H -0.074973 0.286330 0.789894 0.040 Uiso 1 1 calc R U . . .
C8 C 0.1552(5) 0.2229(5) 0.8191(3) 0.0421(9) Uani 1 1 d . . . . .
H8A H 0.236772 0.194291 0.779660 0.063 Uiso 1 1 calc R U . . .
H8B H 0.127668 0.137518 0.843536 0.063 Uiso 1 1 calc R U . . .
H8C H 0.195138 0.310781 0.877912 0.063 Uiso 1 1 calc R U . . .
C22 C 0.4621(4) 0.6296(4) 0.2909(3) 0.0340(8) Uani 1 1 d . . . . .
H22 H 0.514246 0.644708 0.240416 0.041 Uiso 1 1 calc R U . . .
C17 C 0.3341(6) -0.0329(5) 0.1700(3) 0.0511(10) Uani 1 1 d . . . . .
H17A H 0.293176 0.009435 0.112243 0.077 Uiso 1 1 calc R U . . .
H17B H 0.253880 -0.030052 0.210314 0.077 Uiso 1 1 calc R U . . .
H17C H 0.360023 -0.138187 0.143747 0.077 Uiso 1 1 calc R U . . .
C5 C 0.0520(5) 0.6678(6) 0.9446(3) 0.0526(11) Uani 1 1 d . . . . .
H5A H 0.113068 0.754898 0.940190 0.079 Uiso 1 1 calc R U . . .
H5B H 0.123129 0.588095 0.956175 0.079 Uiso 1 1 calc R U . . .
H5C H -0.001295 0.699841 1.001622 0.079 Uiso 1 1 calc R U . . .
C20 C 0.4554(5) 0.3150(7) 0.0516(3) 0.0536(12) Uani 1 1 d . . . . .
H20A H 0.511250 0.303071 -0.004013 0.080 Uiso 1 1 calc R U . . .
H20B H 0.394355 0.405675 0.056374 0.080 Uiso 1 1 calc R U . . .
H20C H 0.383705 0.225340 0.037584 0.080 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H3A O3 H3B 104.5 . . ?
C14 N4 H4 125.5 . . ?
C14 N4 C21 109.1(3) . . ?
C21 N4 H4 125.5 . . ?
C2 N1 H1 125.3 . . ?
C9 N1 H1 125.3 . . ?
C9 N1 C2 109.5(3) . . ?
C13 N2 C10 118.8(3) . . ?
C12 N3 C11 118.0(3) . . ?
C14 C15 C16 127.7(3) . . ?
C18 C15 C14 107.5(3) . . ?
C18 C15 C16 124.8(3) . . ?
N1 C2 C3 108.2(3) . . ?
N1 C2 C1 121.9(3) . . ?
C3 C2 C1 129.9(3) . . ?
N1 C9 C10 117.3(3) . . ?
N1 C9 C6 107.8(3) . . ?
C6 C9 C10 134.9(3) . . ?
N2 C10 C9 116.7(3) . . ?
N2 C10 C11 120.6(3) . . ?
C11 C10 C9 122.7(3) . . ?
N4 C14 C15 107.8(3) . . ?
N4 C14 C13 117.7(3) . . ?
C15 C14 C13 134.5(3) . . ?
N4 C21 C18 108.8(3) . . ?
N4 C21 C22 121.7(3) . . ?
C18 C21 C22 129.4(3) . . ?
C2 C3 C4 125.5(3) . . ?
C2 C3 C6 107.3(3) . . ?
C6 C3 C4 127.2(3) . . ?
C15 C18 C19 127.9(3) . . ?
C21 C18 C15 106.8(3) . . ?
C21 C18 C19 125.3(3) . . ?
O1 C1 C2 125.8(3) . . ?
O1 C1 H1A 117.1 . . ?
C2 C1 H1A 117.1 . . ?
N2 C13 C14 116.1(3) . . ?
N2 C13 C12 120.4(3) . . ?
C12 C13 C14 123.5(3) . . ?
C3 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
C3 C4 C5 112.5(3) . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C15 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
C15 C16 C17 113.8(3) . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C9 C6 C3 107.2(3) . . ?
C9 C6 C7 126.9(3) . . ?
C3 C6 C7 125.9(3) . . ?
N3 C11 C10 120.7(3) . . ?
N3 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
N3 C12 C13 121.4(3) . . ?
N3 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C18 C19 H19A 109.0 . . ?
C18 C19 H19B 109.0 . . ?
C18 C19 C20 112.8(3) . . ?
H19A C19 H19B 107.8 . . ?
C20 C19 H19A 109.0 . . ?
C20 C19 H19B 109.0 . . ?
C6 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C6 C7 C8 112.7(3) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C22 C21 126.1(3) . . ?
O2 C22 H22 116.9 . . ?
C21 C22 H22 116.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 H3A 0.8699 . ?
O3 H3B 0.8696 . ?
O1 C1 1.217(5) . ?
N4 H4 0.8800 . ?
N4 C14 1.364(5) . ?
N4 C21 1.364(4) . ?
N1 H1 0.8800 . ?
N1 C2 1.370(4) . ?
N1 C9 1.368(4) . ?
O2 C22 1.216(5) . ?
N2 C10 1.332(4) . ?
N2 C13 1.331(4) . ?
N3 C11 1.345(5) . ?
N3 C12 1.322(5) . ?
C15 C14 1.401(5) . ?
C15 C18 1.400(5) . ?
C15 C16 1.508(5) . ?
C2 C3 1.395(5) . ?
C2 C1 1.439(5) . ?
C9 C10 1.458(4) . ?
C9 C6 1.406(4) . ?
C10 C11 1.411(5) . ?
C14 C13 1.456(5) . ?
C21 C18 1.388(5) . ?
C21 C22 1.441(5) . ?
C3 C4 1.502(4) . ?
C3 C6 1.406(5) . ?
C18 C19 1.504(4) . ?
C1 H1A 0.9500 . ?
C13 C12 1.412(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.524(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.530(6) . ?
C6 C7 1.508(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.526(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.520(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C22 H22 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 C14 C13 N2 3.3(4) . . . . ?
N4 C14 C13 C12 -176.9(3) . . . . ?
N4 C21 C18 C15 -0.8(3) . . . . ?
N4 C21 C18 C19 178.1(3) . . . . ?
N4 C21 C22 O2 -1.4(5) . . . . ?
N1 C2 C3 C4 177.4(3) . . . . ?
N1 C2 C3 C6 -0.1(3) . . . . ?
N1 C2 C1 O1 -2.0(5) . . . . ?
N1 C9 C10 N2 3.1(4) . . . . ?
N1 C9 C10 C11 -177.9(3) . . . . ?
N1 C9 C6 C3 -0.1(3) . . . . ?
N1 C9 C6 C7 -179.7(3) . . . . ?
N2 C10 C11 N3 2.3(5) . . . . ?
N2 C13 C12 N3 2.2(5) . . . . ?
C15 C14 C13 N2 -176.7(3) . . . . ?
C15 C14 C13 C12 3.1(6) . . . . ?
C15 C18 C19 C20 92.9(5) . . . . ?
C2 N1 C9 C10 -179.4(3) . . . . ?
C2 N1 C9 C6 0.0(3) . . . . ?
C2 C3 C4 C5 -84.0(4) . . . . ?
C2 C3 C6 C9 0.1(3) . . . . ?
C2 C3 C6 C7 179.8(3) . . . . ?
C9 N1 C2 C3 0.0(3) . . . . ?
C9 N1 C2 C1 179.0(3) . . . . ?
C9 C10 C11 N3 -176.7(3) . . . . ?
C9 C6 C7 C8 79.1(4) . . . . ?
C10 N2 C13 C14 178.2(3) . . . . ?
C10 N2 C13 C12 -1.6(5) . . . . ?
C10 C9 C6 C3 179.2(3) . . . . ?
C10 C9 C6 C7 -0.5(6) . . . . ?
C14 N4 C21 C18 0.7(3) . . . . ?
C14 N4 C21 C22 178.4(3) . . . . ?
C14 C15 C18 C21 0.6(3) . . . . ?
C14 C15 C18 C19 -178.2(3) . . . . ?
C14 C15 C16 C17 76.3(5) . . . . ?
C14 C13 C12 N3 -177.6(3) . . . . ?
C21 N4 C14 C15 -0.3(3) . . . . ?
C21 N4 C14 C13 179.7(3) . . . . ?
C21 C18 C19 C20 -85.7(5) . . . . ?
C3 C2 C1 O1 176.7(4) . . . . ?
C3 C6 C7 C8 -100.5(4) . . . . ?
C18 C15 C14 N4 -0.2(3) . . . . ?
C18 C15 C14 C13 179.8(3) . . . . ?
C18 C15 C16 C17 -101.3(4) . . . . ?
C18 C21 C22 O2 175.9(4) . . . . ?
C1 C2 C3 C4 -1.5(5) . . . . ?
C1 C2 C3 C6 -178.9(3) . . . . ?
C13 N2 C10 C9 178.5(3) . . . . ?
C13 N2 C10 C11 -0.5(5) . . . . ?
C4 C3 C6 C9 -177.3(3) . . . . ?
C4 C3 C6 C7 2.4(5) . . . . ?
C16 C15 C14 N4 -178.1(3) . . . . ?
C16 C15 C14 C13 1.9(6) . . . . ?
C16 C15 C18 C21 178.6(3) . . . . ?
C16 C15 C18 C19 -0.2(5) . . . . ?
C6 C9 C10 N2 -176.1(3) . . . . ?
C6 C9 C10 C11 2.9(6) . . . . ?
C6 C3 C4 C5 92.9(4) . . . . ?
C11 N3 C12 C13 -0.4(6) . . . . ?
C12 N3 C11 C10 -1.7(6) . . . . ?
C22 C21 C18 C15 -178.3(3) . . . . ?
C22 C21 C18 C19 0.6(5) . . . . ?
